401900-40-1

Basic information

• Product Name: Andarine
• Synonyms: S-3-(4-acetylamino-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide;N-[4-Nitro-3-(trifluoromethyl)phenyl]-(2S)-3-[4-(acetylamino)phenoxy]-2-hydroxy-2-methylpropanamide;Ostarine;(2R)-3-(4-Cyanophenoxy)-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide;MK-2866;Andarine;Propanamide,3-[4-(acetylamino)phenoxy]-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phe nyl]-,(2S)-;sarM s4
• CAS NO: 401900-40-1
• Molecular Formula: C19H14F3N3O3
• Molecular Weight: 389.3279696
• EINECS: 1308068-626-2
• Product Categories: APIs;Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;SARMS;Inhibitors
• Mol File: 401900-40-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 70-74℃
• Boiling Point: 698.735 °C at 760 mmHg
• Flash Point: 376.381 °C
• Appearance: Pale yellow solid
• Density: 1.47
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.13±0.29(Predicted)
• Water Solubility: 1.2 mg/mL in water
• BRN: 9666695
• CAS DataBase Reference: Andarine(CAS DataBase Reference)
• NIST Chemistry Reference: Andarine(401900-40-1)
• EPA Substance Registry System: Andarine(401900-40-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 401900-40-1(Hazardous Substances Data)

Usage

Selective Androgen Receptor Modulator

Andarine (MK-2866), as the arylpropionamide derivate, has been developed in pharmaceutical industry as a new class of therapeutics called Selective Androgen Receptor Modulator (SARM, either agonists or antagonists at particular androgen receptors) with specific selectivity for particular tissues and organs, that could substitute the synthetic anabolic drugs used in medical treatments.

Clinical Application

The pharmacological activity of andarine suggest the great potential of andarine in the development of the clinically available SARMs, which offers unique therapeutic advantages over their steroidal counterparts and an exciting opportunity to differentially regulate the androgen effects in various target tissues, thus minimizing the interference to normal. Thus, andarine has promising in advanced clinical trials that aim to treat age-related maladies and to counteract symptoms of severe diseases such as sarcopenia and cancer cachexia. However, andarine may be misused in sports where athletes and/or their handlers may seek to gain unfair advantage. Therefore, andarine as agonist is prohibited for use by the International Federation of Horseracing Authorities and the World Anti-Doping Agency.

Biological activity

Andarine is a selective non-steroidal androgen receptor (AR) agonist with Ki of 4 nM, and it is tissue selective for the metabolic organ. Phase 3.

In vitro

In vitro, Andarine binds to androgen receptors with high affinity with Ki of 4 nM. Moreover, 10 nM Andarine stimulated the transcription adjusted by androgen receptor, up to 93%.

In vivo

In vivo, Andarine has an effective metabolic activity, and stimulates the growth of the prostate, seminal vesicle, and levator ani, with ED50 is 0.43 mg/day, 0.55 mg/day, and 0.14 mg/day respectively. This effect is dose dependent. In addition, Andarine acts on FSH, which does not affect some physiological changes caused by castration, and at a dose of 0.5 mg or more per day, partially inhibiting LH production. Andarine was administered to dog intravenously at 0.1, 1, 3, and 10 mg/kg doses, then the total body clearance (CL) decreased from 7.4 mL/min/kg to 3.1 mL/min/kg, the steady-state volume (Vss) was 1.39 L/kg and the half-life was 229 minutes. In addition, Andarine was 10 mg/kg, 1 mg/kg and 0.1 mg/kg, with oral bioavailability of 38%, 62% and 91% respectively. Andarine has tissue selective pharmacological activity and is well treated with 0.5 mg/day concentration, significantly reducing prostate weight to 79.4%.

Characteristics

Andarine is a selective non-steroidal androgen receptor (AR) agonist.

Description

Andarine (S-4) is the arylpropionamide-derived compound [S-3-(4-acetylamino-phenoxy)-2-hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide] first described by Yin et al. to be a selective androgen receptor modulator (SARM). Andarine (S-4) was shown by in vitro and in vivo studies to be an effective anabolic agonist, without side-effects often associated with anabolic-androgenic steroids, relating principally to substrate affinity for 5α-reductase to produce DHT in the prostate. Unfortunately the benefits that SARMs such as andarine (S-4) may provide to clinical medicine have the potential for misuse in sports where athletes and/or their handlers may seek to gain unfair advantage with the assumption that these compounds are undetectable by anti-doping laboratories. SARMs are therefore prohibited for use by the International Federation of Horseracing Authorities and the World Anti-Doping Agency (WADA).

Chemical Properties

Pale Yellow Solid

Uses

It is a potent and tissue-selective androgen receptor modulator (SARM)

Definition

ChEBI: Andarine is an anilide and a member of acetamides. It is a non-steroidal selective androgen receptor modulator.

benefits

Andarine (S4) has a lot of great benefits and this is probably what you are most interested in.The Andarine benefits are:Increased muscle massFat lossFaster recoveryBody recompositionIncreased strength

Side effects

Andarine has gone through quite a bit of research but not as much as other SARMs such as LGD 4033 or Ostarine. From the studies so far and from the anecdotal evidence from people that use it we can tell that there are two side effects.S4 side effects:SuppressionImpaired vision

Regulatory Status

Andarine also named SARM S-4, classified in the S1 class of the WADA prohibited list.US: Andarine is not listed specifically in the Schedules to the US Controlled Substances Act and is not mentioned anywhere on the DEA website.United Nations: The substance is not listed specifically on the Yellow List - List of Narcotic Drugs under International Control nor the Green List - List of Psychotropic Substances under International Control.Canadian Status: Andarine is not currently listed in the CDSA. The substance has been reported to be used for the treatment of muscle wasting, osteoporosis and begning prostatic hyperplaysia and displays androgenic and anabolic activity1-3 . 2 3However, since andarine is not a steroid, it cannot be included uner item 23 of Schedule IV to the CDSA.

references

[1]. yin, d., et al., pharmacodynamics of selective androgen receptor modulators. j pharmacol exp ther, 2003. 304(3): p. 1334-40.[2]. thevis, m., et al., mass spectrometric characterization of urinary metabolites of the selective androgen receptor modulator s-22 to identify potential targets for routine doping controls. rapid commun mass spectrom, 2011. 25(15): p. 2187-95.

InChI:InChI=1/C19H18F3N3O6/c1-11(26)23-12-3-6-14(7-4-12)31-10-18(2,28)17(27)24-13-5-8-16(25(29)30)15(9-13)19(20,21)22/h3-9,28H,10H2,1-2H3,(H,23,26)(H,24,27)/t18-/m1/s1

Upstream product

• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 103-90-2 4-acetaminophenol 
• 216665-24-6 (S)-(-)-3-bromo-2-hydroxy-2-methyl-N-[(4-nitro-3-trifluoromethyl)phenyl]propanamide 
• 206193-18-2 N-[4-nitro-3-(trifluoromethyl)phenyl]-(2R)-3-bromo-2-hydroxy-2-methylpropanamide 
• 348597-81-9 (S)-N-(4-nitro-3-(trifluoromethyl)phenyl)-2-methyloxirane-2-carboxamide 

Relevant articles and documents

Synthetic method of alpha-hydroxypropanamide derivatives with optical activity

The invention discloses a synthetic method of alpha-hydroxypropanamide derivatives with optical activity and belongs to the field of organic synthesis. Proline taken as a chiral auxiliary, as well asmethacryloyl chloride, is subjected to acylation, bromination and chiral auxiliary removal, a product and 4-cyano-3-trifluoromethylaniline are subjected to nucleophilic substitution, and 3-bromo-2-hydroxy-2-methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]propanamide is obtained and subjected to nucleophilic substitution with 4-cyanophenol, and the compound 3-(4-cyanophenoxy)-N-[4-cyano-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. 3-bromo-2-hydroxy-2-methyl propionic acid and 4-nitro-3-trifluoromethylaniline are subjected to aminolysis, a product is subjected to nucleophilic substitution with paracetamol, and the compound 3-(4-acetoxyphenoxy)-N-[4-nitro-3-(trifluoromethylphenyl]-2-hydroxy-2-methylpropanamide with optical activity is prepared. The efficient synthetic method of the alpha-hydroxypropanamide derivatives with optical activity is provided.

PRODRUGS OF SELECTIVE ANDROGEN RECEPTOR MODULATORS AND METHODS OF USE THEREOF

The present invention provides prodrugs of selective androgen receptor modulators (SARMs), and their use in treating or reducing the incidence of osteoporosis, a variety of hormone-related conditions, conditions associated with Androgen Decline in Aging Male (ADAM); conditions associated with Androgen Decline in Female (ADIF), and muscular wasting conditions, obesity, dry eye conditions, and prostate cancer. The prodrugs are also useful in oral androgen replacement therapy and male contraception.

Design, Synthesis, and Biological Characterization of Metabolically Stable Selective Androgen Receptor Modulators

A series of nonsteroidal ligands were synthesized as second-generation agonists for the androgen receptor (AR). These ligands were designed to eliminate metabolic sites identified in one of our first-generation AR agonists, which was inactive in vivo due